EP0051563A1 - Composés monoazoiques - Google Patents

Composés monoazoiques Download PDF

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Publication number
EP0051563A1
EP0051563A1 EP81810423A EP81810423A EP0051563A1 EP 0051563 A1 EP0051563 A1 EP 0051563A1 EP 81810423 A EP81810423 A EP 81810423A EP 81810423 A EP81810423 A EP 81810423A EP 0051563 A1 EP0051563 A1 EP 0051563A1
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EP
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Prior art keywords
radical
alkyl
optionally substituted
monoazo compounds
formula
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EP81810423A
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German (de)
English (en)
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EP0051563B1 (fr
Inventor
Hansrudolf Dr. Schwander
Christian Dr. Zickendraht
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Novartis AG
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Ciba Geigy AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
    • C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0801—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls
    • C09B29/0803—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls containing SO3H, OSO3H

Definitions

  • the invention relates to new monoazo compounds, their mixtures with one another, processes for their preparation and their use as dyes for dyeing and printing textile materials, especially wool and polyamide.
  • the new monoazo compounds correspond to Formula I
  • R, R 2 and R 3 are to be combined with one another in such a way that the molecule in R, R 2 or R 3 contains a sulfo group or in R a sulfato group.
  • R is a phenyl or naphthyl radical, it can, for example, also carry an alkyl substituent (C 1 -C 4 ). If R stands for an alkyl radical, this can be unbranched or branched, with a chain length of up to 8 carbon atoms. Examples of alkyl radicals are methyl, ethyl, n- and iso-propyl, n-, sec- or tert-butyl, n- or iso-pentyl, n-hexyl, n-heptyl , n- or iso-octyl or the 2-ethylhexyl radical.
  • the alkyl radical can be substituted, the substituents being, for example, the phenyl radical, which in turn can be further substituted by, for example, a sulfo group, the cyano group or a halogen atom, such as a chlorine atom.
  • R is a cycloalkyl radical, medium ring sizes such as the cyclopentyl, hexyl or heptyl radical are suitable; the cyclic radical can be substituted by, for example, alkyl (C 1 -C 4 ).
  • R is a propenyl radical which is optionally substituted by a halogen atom, such as a chlorine or bromine atom, it is, for example, the propenyl, 3-chloroprop-2-enyl, 2-chloro or 2-bromo-prop- 2-enyl radical.
  • a halogen atom such as a chlorine or bromine atom
  • R denotes the cyclohexyl radical which is optionally substituted by one or more methyl groups, or the benzyl or ⁇ -phenethyl radical, the phenyl nucleus of which may be further substituted by a sulfo group.
  • X is a halogen atom, it is the fluorine, chlorine, bromine or iodine atom, with the bromine atom being preferred.
  • R 1 in the meaning of alkyl (C 1 -C 4 ) represents a branched, but preferably unbranched alkyl radical, such as the methyl, ethyl, n- and iso-propyl or n-, sec- or tert-butyl radical. Of these, the methyl radical is preferred.
  • R 2 is an alkyl radical having 1 to 8 carbon atoms, it is an unbranched or branched alkyl radical, such as, for example, methyl, ethyl, n- and isopropyl, n-, sec- or tert. -Butyl, red or iso-pentyl, n-hexyl, n-heptyl, n- or iso-octyl or the 2-ethylhexyl radical.
  • the lower alkyl radicals (C 2 -C 4 ) are preferred.
  • R 2 stands for a sulfatoalkyl radical (C 1 -C 4 ) or a sulfoalkyl radical (C 1 -C 4 ), the ethyl sulfate, sulfoethyl and sulfopropyl radicals are particularly suitable.
  • R 2 denotes a cycloalkyl radical, it means such a medium ring size as, for example, the cyclopentyl, hexyl or heptyl radical.
  • R 2 represents the ethyl radical.
  • R 3 in the meaning of alkyl (C 1 -C 4 ) represents a branched, but preferably unbranched alkyl radical, such as the methyl, ethyl, n- and iso-propyl or n-, sec.- or tert.- Butyl residue. If R 3 is a cycloalkyl radical, medium ring sizes such as the cyclopentyl, hexyl or heptyl radical are suitable; these radicals can be mono- or polysubstituted by a lower alkyl radical (C 1 -C 4 ), preferably the methyl group. R 3 is an alkylene Rest, so that is especially so
  • Benzyl and the ß-phenethyl radical meant.
  • the phenyl nucleus of these residues can be substituted by a sulfo group.
  • Monoazo compounds in which R 3 has the meaning of a sulfobenzyl or ⁇ -sulfophenethyl radical are preferred.
  • the azo bridge is in the p-position to one of the two carbonyl groups.
  • the invention also relates to the mixtures of isomeric compounds of this formula.
  • the invention relates both to monoazo compounds of the formula I in which the azo bridge is in the o or p position to one of the two carbonyl groups of the phthalimide radical, and to their mixtures with one another, e.g. a mixture of a monoazo compound of the formula I in which the azo bridge is bonded in the p-position to one of the carbonyl groups with a monoazo compound of the formula I in which the azo bridge is bonded in the o-position to one of the carbonyl groups.
  • the radical R is, for example an optionally alkyl substituted phenyl (C 1 -C 4) or naphthyl radical, an unsubstituted or substituted by alkyl (C 1 -C 4) cycloalkyl, optionally substituted by cyano, halogen or phenyl alkyl (C 1 - C 8 ) or a propenyl radical optionally substituted by halogen, the following possible combinations are possible for the radicals R 2 and R 3 : R 2 is an alkyl or cycloalkyl radical and R 3 is an alkylene or R2 is a sulfatoalkyl (C 1 -C 4 ) or sulfoalkyl (C 1 -C 4 ) radical and R 3 is an alkylene , Alkyl (C I
  • the radical R contains a sulfo group, for example an alkyl radical (C 1 -C 8 ) substituted by sulfophenyl, preferred
  • Residues are the sulfobenzyl, or the ß-sulfophenethyl or the rest of the formula for example
  • R 2 is an alkyl radical (C 1 -C 8 ), in particular ethyl, or a cycloalkyl radical, in particular cyclohexyl
  • R 3 is an alkyl radical (C 1 -C 4 ), in particular ethyl, one optionally substituted by alkyl (C 1 -C 4 ), especially methyl, substituted cycloalkyl, especially cyclohexyl, or one
  • R is an optionally alkyl substituted phenyl (C 1 -C 4), optionally substituted by alkyl (C 1 -C 4) substituted cyclohexyl group, a substituted optionally substituted by cyano, phenyl or sulfophenyl alkyl (C 1 - C 8 ) or a propenyl radical optionally substituted by halogen.
  • R 2 is an unsubstituted alkyl radical (C 2 -C 8 ) or cyclohexyl and R 3 is an alkylene.
  • R 2 is sulfoethyl, sulfopropyl or ethyl sulfate and R is unbranched or branched alkyl (C 1 -C 4 ), Alkylene or cyclohexyl optionally substituted by methyl.
  • R is preferably ethyl sulfate and R 3 is ethyl.
  • R denotes a cyclohexyl radical which is optionally substituted by one or more methyl groups, the benzyl or ⁇ -phenethyl radical, or an unbranched or branched alkyl (C 2 -C 8 ) radical, and R 2 is ethyl, octyl or cyclohexyl and R 3 is the alkylene or R 2 is ethyl sulfate, sulfoethyl or sulfopropyl and R 3 is alkylene. or cyclohexyl optionally substituted by methyl.
  • Monoazo compounds of the formula I in which R is cyclohexyl are also preferred.
  • the isomer mixtures of the monoazo compounds of the formulas are particularly preferred and as well as the monoazo compound of the formula
  • the monoazo compounds of the formula I according to the invention can be prepared in a manner known per se, for example in such a way that an amine of the formula II diazotized and with a coupling component of formula III couples.
  • the symbols R, X, R 1 , R 2 and R3 have the meaning given, with the condition that one of the radicals R, R and R 3 contains a sulfo group or the radical R Z contains a hydroxy group. If the radical R 2 is substituted by a hydroxyl group, this is esterified after coupling with, for example, sulfamic acid to give the sulfato group.
  • One procedure is characterized in that an amine of the formula II which contains no sulfo group in the radical R is diazotized and coupled to a coupling component of the formula III in which R 2 is an alkyl (C 1 -C 8 ) or cycloalkyl radical and R 3 an alkylene [Radical means or wherein R 2 is a hydroxyalkyl (C 1 -C 4 ) or sulfoalkyl (C 1 -C 4 ) radical and R 3 is an alkylene Radical, an alkyl radical (C 1 -C 4 ) or a cycloalkyl radical which is optionally substituted by alkyl (C 1 -C 4 ) and, if appropriate subsequently, if R 2 contains a hydroxyl group, this is esterified to the sulfato group.
  • a further procedure is characterized in that an amine of the formula II, in which R is a sulfophenyl-substituted alkyl radical (C 1 -C 8 ), is diazotized and coupled to a coupling component of the formula III, in which R 2 is an alkyl radical (C 1 - C 8 ) or a cycloalkyl radical and R 3 is an alkyl radical (C 1 -C 4 ), an optionally substituted by alkyl (C -C) cycloalkyl radical or an alkylene Rest is.
  • Amines of the formula II are preferably used, in which R is a phenyl radical which is optionally substituted by alkyl (C 1 -C 4 ), a cyclohexyl radical which is optionally substituted by alkyl (C -C), an alkyl radical which is optionally substituted by cyano, phenyl or sulfophenyl (C 1 - C 8 ) or an optionally substituted halogen by propenyl and X has the meaning given under formula II, in particular hydrogen or bromine.
  • Another preferred process is characterized in that an amine of the formula II which contains no sulfo group in the radical R is diazotized and coupled to a coupling component of the formula III, in which R 1 is hydrogen or methyl, R 2 is an unsubstituted alkyl radical (C 2 - C 8 ) or cyclohexyl and R 3 is an alkylene.
  • R 2 sulfoethyl, sulfopropyl or hydroxyethyl and R 3 unbranched or branched alkyl (C 1 -C 4 ), alkylene or cyclohexyl optionally substituted by methyl, and then optionally if R 2 contains a hydroxyl group, esterifies it to the sulfato group.
  • a likewise preferred process is characterized in that an amine of the formula II in which R is a sulfobenzyl or ⁇ -sulfophenethyl radical or a radical of the formula and X is hydrogen or bromine, diazotized and coupled to a coupling component of the formula III, in which R 1 is hydrogen or methyl, R 2 is ethyl and R 3 is ethyl or the benzyl or ⁇ -phenethyl radical.
  • Another particularly preferred process is characterized in that amines of the formula II are used in which R is cyclohexyl.
  • the preferred mixture of isomers of the monoazo compounds of the formulas is obtained by diazotizing an isomer mixture of 3-amino and 4-amino-N-cyclohexyl-phthalimide and coupling it to N-ethyl-N-sulfophenethyl-3-methylaniline.
  • the also preferred monoazo compound of the formula is made by diazotizing 4-amino-N-sulfophenethyl phthalimide and coupling to N-ethyl-N-benzyl-3-methylaniline.
  • aminophthalimide derivatives whose N substituent has a sulfo group are 3- or 4-amino-N- [ß-sulfophenethyl] phthalimide and 3- or 4-amino-N- [a-sec.-butyl-y- called sulfophenyl-propyl] phthalimide.
  • analog 3-aminophthalimide derivatives or their mixtures with 4-aminophthalimide derivatives can also be used.
  • the new monoazo compounds of the formula I are used above all as dyes for dyeing and printing textile materials which can be dyed with anionic dyes, especially polyamide materials and wool.
  • the dyeing can be carried out by any continuous or discontinuous methods suitable for the corresponding substrate (e.g. exhaust, padding or printing processes).
  • the e rfindungsgemässen Monoazo.farbstoffe characterized in dyeing processes at pH 6 by a high degree of exhaustion, good Migrating and the dyeing of polyamide with good ceiling of streaking out.
  • the dyeings obtained with the dyes of the formula I have good general fastness properties, such as, above all, very good wet fastness, good light fastness and good formaldehyde resistance.
  • the colorants are good hard water resistant and have a high water solubility. Furthermore, they show good results in combination dyeing with monosulfonic acid dyes, which are dyed at pH 6.
  • the textile materials to be dyed can be in a wide variety of processing forms, such as knitted fabrics, fabrics, yarns and fibers, and finished articles, such as shirts.
  • Example 1 42 parts of 4-nitrobenzene-1,2-dicarboxylic acid are stirred in 120 parts of glacial acetic acid at room temperature and 36 parts of cyclohexylamine are added dropwise to the suspension formed in this way. The temperature rises to 45 ° C and a clear solution is obtained. The solution is refluxed for a further two hours and then added to 1000 parts of water. The deposited 4-nitro-N-cyclohexyl phthalimide is filtered off, dissolved in 150 parts of dimethylformamide and hydrogenated with palladium-carbon as a catalyst. This gives the amine of the formula which can be separated from the previously filtered hydrogenation solution by adding water. After filtering and drying, a light yellow powder with a melting point of 192-193 ° C is obtained.
  • Example 20 21 parts of the isomer mixture 3- and 4-nitrophthalic acid, obtained by nitrating phthalic acid, are dissolved in 100 parts of glacial acetic acid, 15 parts of cyclohexylamine are added and the mixture is stirred under reflux for four hours. Then the glacial acetic acid is distilled off in vacuo, the residue is dissolved in 100 parts of dimethylformamide and hydrogenated with palladium-carbon as a catalyst. The mixture of the isomeric amines of the formulas becomes from the solution filtered off from the catalyst deposited in good yield by dilution with water as a light yellow powder.
  • Example 21 30 parts of the compound given in Table 1 under 7, column III are suspended in 300 parts of carbon tetrachloride, 30 parts of N-bromosuccinimide are added and the mixture is then stirred for 4 hours and boiled under reflux. For working up, the mixture is filtered and the residue is recrystallized from glacial acetic acid.
  • the product has the formula: Mp 181-183 ° C
  • Example 22 38.5 parts of 4-nitrophthalimide, 14 parts of potassium carbonate and 45 parts of 2,3-dichloropropene are stirred in 100 parts of dimethylformamide at 80 ° C. for 24 hours.
  • the reaction mixture is worked up in 1000 parts of water.
  • the product which separates out is filtered off and then redissolved in 200 parts of glacial acetic acid.
  • 38 parts of iron powder are added to the solution at 50 ° C., the reduction commencing with significant heat development.
  • the iron powder is filtered off and the filtrate is diluted with water, the amine of the following formula precipitating: M.p. 165-167 ° C.
  • Example 25 To a mixture consisting of 38.4 g of 4-nitrophthalimide, 13.3 g of acrylonitrile and 15 ml of dimethylformamide, 0.4 ml of 50% potassium hydroxide solution is added at 60 ° C. The temperature is then raised to 120 ° C. and the mixture is stirred at this temperature for about 30 minutes until the reaction has ended completely owing to the thin-layer chromatogram. To isolate the product, pour the still hot solution onto cold water and filter the precipitated product of the formula and wash off with water. The amino compound of the formula is obtained by catalytic hydrogenation
  • Example 26 To a mixture consisting of 5 g of the compound of the formula 6 ml of 36% hydrochloric acid are added in finely divided form and 30 ml of isopropanol at 0 ° C. 5 ml of 4N nitrite solution are slowly added dropwise to this mixture at a temperature of 0-2 ° C. below the level. The mixture is stirred for a further 30 minutes in the cold and then 0.4 g of urea are added to the reaction mixture. After a further 15 minutes, the mixture is added to a neutral solution of 2/100 mol of the compound of the formula which is present as the sodium salt, in 100 ml of water. The pH of the reaction mixture is adjusted to 3 by adding ammonium acetate and the mixture is stirred at 0-5 ° C. until the coupling has ended. For working up, the pH is reduced to 2 and the precipitated product is isolated by filtration.
  • the slurry is then slurried in 150 ml of water, adjusted to pH 7, and the precipitated sodium salt of the dye of the formula is filtered and dry the product in vacuo at 70 ° C. A red powder is thus obtained, which dissolves in water with a red color.
  • BeipH 6 dyed on polyamide this dye gives red dyeings which have good wet fastness properties and good light fastness.
  • the dye shows a good structure and a high degree of exhaustion, furthermore good migration behavior and good covering of the streakiness.
  • the dyes listed in Table 3 are obtained in an analogous manner and also dye polyamide from a weakly acidic bath in red shades with good fastness properties.
  • Example 66 A mixture consisting of 4.90 g of isomeric compounds of the formulas 30 ml of isopropanol and 6 ml of 36% hydrochloric acid are slowly mixed with 5 ml of a 4N sodium nitrite solution, the temperature being kept at 0-2 ° C. The mixture is then stirred at the same temperature for 1 hour, after which 0.40 g of urea is added. After a further 15 minutes, the diazo solution is allowed to run into a neutral solution of 2/100 mol of N-benzyl-N-ethyl-m-toluidine-sulfonic acid in 100 ml of water, the pH being adjusted by adding 30% ammonium acetate solution holds at 3-4.
  • the mixture is heated to 90 ° and 10% by volume of sodium chloride is added, the mixture is then allowed to cool and the mixture is isolated by filtration.
  • the suction filter is suspended in 30 ml of water, 50 ml of 2N hydrochloric acid are added and the mixture is heated to 90 °, the dye mixture separating out as an oil. It is decanted off and the residue is dissolved again with 50 ml of water, whereupon it is again precipitated with 10 ml of 2N hydrochloric acid at 90 °. After decanting, the residue is dissolved in 200 ml of water, the pH is adjusted to 7.0 with sodium hydroxide solution and the dye mixture is isolated by evaporation in vacuo.
  • the dye mixture containing the dyes of the formulas is a red powder that easily dissolves in water with a red color.
  • the red dyeings produced with this dye mixture on polyamide material are good light and wet fast, furthermore the dye mixture shows a good migration and good covering of the streakiness.
  • Example 26 If the azo coupling is carried out as described in Example 26 and the bromine-containing phthalimide derivatives of Example 21 are used as the diazo component, the dyes of the following Table 5 are obtained. These dyes dye polyamide from a weakly acidic bath in bluish-red shades, which are good Have authenticity properties.
  • Example 86 A mixture consisting of 8.1 g of the compound of the formula is stirred (obtained by coupling N-cyanoethyl-4-aminophthalimide to N-ethyl-N-hydroxyethyl-m-toluidine), 7.75 g of sulfamic acid and 30 ml of pyridine for 30 minutes at a temperature of 98-100 ° C, whereupon the pyridine is removed on the rotary evaporator in a vacuum as completely as possible. The residue is taken up in 20 ml of water, adjusted to pH 7 with sodium hydroxide solution and again evaporated to dryness in vacuo. The residue is dried in a drying cabinet in a vacuum at 70 ° C. The sodium salt of the dye of the formula thus obtained dissolves in water with a red color.
  • the red dyeings available with this dye from an acidic bath on polyamide are good lightfast.
  • the dyes listed in Tables 6 and 7 below are obtained in an analogous manner and dye polyamide from acidic bath in red shades with good fastness properties. If, in the preceding examples, which are derived from 4-aminophthalimide derivatives, equivalent amounts of the corresponding 3-aminophthalimide derivatives are used, the dyes of the following tables are obtained using an otherwise identical procedure (see Examples 26 and 86) 8 and 9, which have similar properties to the corresponding dyes derived from 4-aminophthalimide derivatives. Said dyes also dye polyamide from an acid bath red with comparable fastness properties.
  • Example 145 A mixture consisting of 5.35 g of the compound of the formula is stirred and 50 g of oleum 10% S0 3 content for 6 hours at 20-25 ° C, whereupon the mixture is poured onto a mixture of 80 g of ice and 20 ml of water.
  • the precipitated sulfonic acid of the formula is filtered off and squeezed well.
  • slurry in 75 ml of water adjust to pH 7 with sodium hydroxide solution and add 5 ml of 4N nitrite solution.
  • This mixture is allowed to run in with good stirring at 0-2 ° C. to a mixture consisting of 40 g of ice, 10 ml of 36% hydrochloric acid and 0.10 ml of 4N nitrite solution, followed by stirring at 0-2 ° C. for 1 hour. Excess nitrite is destroyed by adding sulfamic acid.
  • a solution is prepared by adding hydrochloric acid to a mixture of 4.70 g of N-benzyl-N-ethyl-m-toluidine and 20 ml of water, which solution is added to the diazo suspension obtained above.
  • the pH is adjusted to 3-3.5 by adding sodium hydroxide solution and the mixture is stirred at 0-5 ° C. until the coupling has ended.
  • the dye is isolated by acidification with hydrochloric acid, then suspended in water and, after neutralization with sodium hydroxide solution, isolated in the usual way by salting out.
  • the dye of the formula obtained forms a red powder after drying, which dissolves in water with a red color. The red dyeings created with this dye on polyamide materials are good light and wet fast.
  • the same amount of a mixture of isomers that the amines of the formulas are used for contains (obtained analogously to the benzyl compound described by reacting ⁇ -phenylethylamine and nitrophthalic acid mixture in glacial acetic acid, hydrogenating the nitrofunction and finally sulfonating the phenyl radical),
  • the dyes in Table 12 are obtained in an analogous procedure, which polyamide at pH 6 in wet and dye lightfast tones and which have a high degree of exhaustion.
  • Example 155 A dyebath is prepared from 4000 parts of water, 4 parts of ammonium acetate, 2 parts of the dye according to Example 26 and enough acetic acid that the pH of the bath is 6. The resulting dye bath is mixed with 100 parts of a synthetic polyamide tricot, heated to boiling within half an hour and dyed at 100 ° C. for 45 minutes. A red color is obtained with good wet fastness properties.
  • Example 156 100 parts of wool knitting yarn are introduced at 50 ° C. into a dyebath containing 2 parts of the dye of Example 26, 4 parts of ammonium sulfate and 2 parts of a leveling aid per 4000 parts of water. The liquor is brought to the boil over the course of 45 minutes and kept at the boiling temperature for a further 45 minutes. The material to be dyed is then removed, thoroughly rinsed with cold water and dried. A red wool dyeing with good fastness properties is obtained.

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EP81810423A 1980-10-30 1981-10-26 Composés monoazoiques Expired EP0051563B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH8074/80 1980-10-30
CH807480 1980-10-30

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EP0051563A1 true EP0051563A1 (fr) 1982-05-12
EP0051563B1 EP0051563B1 (fr) 1985-04-24

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US (1) US4734490A (fr)
EP (1) EP0051563B1 (fr)
JP (1) JPS57102953A (fr)
DE (1) DE3170172D1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004044058A1 (fr) * 2002-11-11 2004-05-27 Ciba Specialty Chemicals Holding Inc. Colorants a base de phthalimidyle azo, procede de preparation et utilisation
EP2754696A1 (fr) 2013-01-15 2014-07-16 DyStar Colours Distribution GmbH Mélanges de colorants disperse bleu marine et noir sans AOX
US9493657B2 (en) 2013-01-14 2016-11-15 Dystar Colours Distribution Gmbh AOX-free navy and black disperse dyes

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6008332A (en) * 1994-02-11 1999-12-28 Ciba Specialty Chemicals Corporation Phthalimidylazo dyes, process for their preparation and the use thereof
TW353105B (en) * 1994-05-30 1999-02-21 Ciba Sc Holding Ag Reactive dyes, their preparation and use
CN1245516A (zh) * 1996-11-27 2000-02-23 伊斯曼化学公司 制备吸光聚合物组合物的方法
DE102006027535A1 (de) * 2006-06-14 2007-12-20 Dystar Textilfarben Gmbh & Co. Deutschland Kg Dispersionsfarbstoffe, ihre Herstellung und ihre Verwendung

Citations (3)

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Publication number Priority date Publication date Assignee Title
FR2018862A1 (fr) * 1968-09-25 1970-06-26 Basf Ag Colorants monoazoiques sulfones
FR2080423A5 (en) * 1970-01-19 1971-11-12 Crompton & Knowles Corp Water-soluble dyes and dye intermediates
GB1504795A (en) * 1976-01-23 1978-03-22 Yorkshire Chemicals Ltd Water-soluble monoazo dyes derived from n-substituted aminophthalimide diazo components

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Publication number Priority date Publication date Assignee Title
US3551407A (en) * 1967-04-19 1970-12-29 Basf Ag Monoazo dyes derived from aminophthalimides
GB1343543A (en) * 1970-01-19 1974-01-10 Crompton & Knowles Corp Mono-and dis-azo dyestuffs containing 3-sulpho-propylamino groups
BE793232A (fr) * 1971-12-23 1973-06-22 Basf Ag Colorants derives du phtalimide
US3980634A (en) * 1973-07-02 1976-09-14 Eastman Kodak Company Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith
US4255326A (en) * 1979-03-30 1981-03-10 Eastman Kodak Company Nitrogen and/or sulfur containing heterocyclic azo dyes with aniline, tetrahydroquinoline and benzomorpholine couplers having sulfate group
US4267104A (en) * 1979-06-14 1981-05-12 Eastman Kodak Company Dyes from selected substituted aniline diazo components and aniline couplers containing sulfate ester groups

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2018862A1 (fr) * 1968-09-25 1970-06-26 Basf Ag Colorants monoazoiques sulfones
FR2080423A5 (en) * 1970-01-19 1971-11-12 Crompton & Knowles Corp Water-soluble dyes and dye intermediates
GB1504795A (en) * 1976-01-23 1978-03-22 Yorkshire Chemicals Ltd Water-soluble monoazo dyes derived from n-substituted aminophthalimide diazo components

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004044058A1 (fr) * 2002-11-11 2004-05-27 Ciba Specialty Chemicals Holding Inc. Colorants a base de phthalimidyle azo, procede de preparation et utilisation
US9493657B2 (en) 2013-01-14 2016-11-15 Dystar Colours Distribution Gmbh AOX-free navy and black disperse dyes
US9534118B2 (en) 2013-01-14 2017-01-03 Dystar Colours Distribution Gmbh High wet fast disperse dye mixtures
EP2754696A1 (fr) 2013-01-15 2014-07-16 DyStar Colours Distribution GmbH Mélanges de colorants disperse bleu marine et noir sans AOX

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JPS57102953A (en) 1982-06-26
US4734490A (en) 1988-03-29
DE3170172D1 (en) 1985-05-30
EP0051563B1 (fr) 1985-04-24
JPH0411587B2 (fr) 1992-02-28

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